Holiday houses in Middlesex County

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Top-rated holiday rentals in Middlesex County

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Superhost
An outdoor seating area features dark wicker furniture with bright turquoise cushions, providing a comfortable space for relaxation. The view includes a landscaped yard with palm trees and a swimming pool, outlined by a wooden pergola and surrounded by vibrant greenery.
Home in Portmore
4.86 out of 5 average rating, 214 reviews

🏝🏝HIDDEN GEMS 💎 💎 🏝🏝 Vacation Home 🏡🏞

This carefully designed house is ideal for persons looking for a cool refreshing modern and comfortable vacation stay . It is perfectly located in quiet and secure gated community Phoenix park village ,in the well developed sunshine city of portmore st catharine . It is most suitable for you because of its convenient access to all it has to offer around it ,its famous helshure beach, movie theater ,shopping malls ,clubs ,restaurants etc . it is the place for families ,couples, or just friends

Top Guest favourite
A serene outdoor space is showcased, featuring a shaded gazebo surrounded by palm trees and manicured greenery. In the background, a swimming pool is visible, with residential buildings partially framed by the lush hillside.
Condo in Ocho Rios
4.92 out of 5 average rating, 114 reviews

The Ocean Ridge - Ocho Rios, Stunning Sea Views

The Ocean Ridge Apartment (K1), Sky Castles, Columbus Heights, in Ocho Rios. With jaw-dropping views of the sea & cruise ships, this studio unit was renovated in 2023 & is ideally located for a relaxing getaway, remote work, or a long vacation. The unit is bright & uncluttered with a tastefully modern décor. K1 is located in a gated hillside complex, close to all major attractions, some walkable. The area provides unparalleled scenic views of the sea, mountains & flora of a tropical paradise.

Guest favourite
A serene ocean view is presented, with gentle waves lapping at the shore. Lush green lawn stretches towards the water, bordered by ornamental shrubs. A large tree provides shade, enhancing the natural beauty of the tranquil landscape under a clear blue sky.
Apartment in Ocho Rios
4.85 out of 5 average rating, 184 reviews

Precious Studio with a Vast Ocean View

We are fully operational post Hurricane Melissa with power, water & wifi Unwind at this stunning ocean-view studio only 5 minutes away from the heart of Ocho Rios. The studio is freshly renovated with granite counter tops in the kitchen and bathroom, and porcelain tile throughout for a luxurious yet homey feel. Enjoy the vast ocean view and dip your toes in the water only a few steps out from the patio. This studio is the perfect place for relaxing, listening to the ocean and enjoying the breeze

Guest favourite
A semi-open living area is presented with white walls and modern furnishings. A wooden coffee table sits in front of a comfortable sofa. Large windows overlook the sea, revealing two loungers on the balcony, creating a serene atmosphere with natural light.
Condo in Ocho Rios
4.83 out of 5 average rating, 276 reviews

Seafront Apartment nxt to Beach

My place is in Ocho Rios Jamaica , walking distance from Ocho Rios Town centre . Its a homely seafront, split level apartment within a traditional 1960s style past resort directly next to Mahogany beach. Breathtaking sea views, set within a beautiful garden. The people are lovely and the sea and beach/bar are so relaxing. You can book and set sail from the beach on a Cool Runnings catamaran cruise. My place is good for couples, solo adventurers, business travellers, and families (with kids)

Guest favourite
A spacious living area is furnished with a comfortable sofa and an armchair, arranged around a wooden coffee table. Natural light enters through large glass doors adorned with shutters. Plants and decor items add a touch of greenery, enhancing the serene ambiance of the space.
Condo in Ocho Rios
4.77 out of 5 average rating, 118 reviews

Spectacular Sea Spot. Perfect for work or vacation

The condominium at Carib Ocho Rios is a quaint and beautiful, fully-furnished ocean front, 1 bedroom, 1 bathroom condominium located on the edge of the hub in Ocho Rios. The ocean beckons you as you relax on the patio. The beautiful salt & fresh water ocean view pools and the sound of the ocean awaits you. The apartment offers all the amenities to ensure your stay is relaxing and comfortable. It is located in a 24 hr gated community and a 5 minutes walk to restaurants, a bar and supermarket.

Top Guest favourite
A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.
Bungalow in Laughlands District
4.89 out of 5 average rating, 192 reviews

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

Guest favourite
A private gazebo offers a spacious seating area with a glass-top table and dark wicker chairs. The structure features a white lattice design, framing sweeping ocean views and a vibrant sunset. Surrounding greenery enhances the tranquil atmosphere.
Condo in Ocho Rios
4.88 out of 5 average rating, 257 reviews

One of Ocho Rios Best Getaway Airbnb!

Welcome to Marazul, a picturesque vacation condo at upscale Columbus Heights in the hills of Ocho Rios. The perfect gateway with postcard-like panoramic ocean views and all the amenities to make your stay feel right at home. Surrounded by beautifully manicured rainforest gardens and direct access to 1 of 5 community pools. For your convenience, we are centrally located near restaurants, beaches, and the most popular attractions in the area only minutes away. Do you see yourself here?

Guest favourite
A traditional wooden cottage sits amidst lush tropical vegetation. Its front porch features wooden railings, and a pathway of gravel leads to the entrance. Surrounding foliage includes tall plants and trees, creating a serene and natural atmosphere.
Cabin in Oracabessa
4.94 out of 5 average rating, 52 reviews

Papa Curvin's Cottages & Seaside Tropical Garden 1

From the STAR deck or laying in the hammock you will be able to enjoy the beautiful view of the sea on the propety, or discover exotic birds and butterflies in the lush vegetation. In the evenings you can watch the light of fireflies. If you want to, you can fish directly on the property or get refreshed by jumping from the cliffs into the sea, if the sea conditions allow. Enjoy our sun deck overlooking the cliffs giving you a panoramic view of the ocean. And: Visit our CAVE!

Superhost
A verandah offers a serene space with two comfortable chairs and a small table. A stack of books rests on the table beside a cup, with views of the ocean and palm trees in the background, enhancing a peaceful atmosphere.
Condo in Tower Isle
4.83 out of 5 average rating, 187 reviews

2 bedroom Oceanfront condo with a pool

Kick back and relax in this calm, stylish 2 bedroom Condo on the ocean with an infinity pool. We are approx 5 minutes east of Ocho Rios and within walking distance to a local jerk centre & bar, PG's Italian restaurant and a grocery store. We can host up to four guests. As we have many couples traveling we offer a discounted base rate for two guests and then each additional guest comes with an additional fee up to a maximum of four.

Top Guest favourite
The bright living area features a single day bed with striped bedding, accented by floral pillows. A light-colored coffee table sits in front, surrounded by modern furniture. A large window offers a view of the Caribbean Sea, while greenery adds a fresh touch to the space.
Condo in Ocho Rios
4.99 out of 5 average rating, 226 reviews

Carib Escape Water-Front Condominium Ocho Rios

Hurricane Melissa update - All services are up and running. Most restaurants and attractions are open in Ochi and eastern parishes and we are ready to welcome you back.❤️❤️❤️ 180 degree view of the Caribbean Sea. Fully refurbished, modern chic Ocean Front Condo. Great Location in the Heart of Ocho Rios. Close to Restaurants, Attractions, Shops and right next to Mahogany Beach. Gated community with 24 hours security.

Top Guest favourite
A welcoming entrance features a charming archway and decorative columns, leading to a well-maintained facade. The property is set against a backdrop of rolling hills, with a paved driveway and lush greenery surrounding the area, creating a tranquil and inviting first impression.
Home in Mandeville
5 out of 5 average rating, 63 reviews

RUSTIK INN cozy home away from home

I’m pleased to welcome guests to my cozy abode dubbed Rustik Inn. Nestled in lush green vegetation, you’ll find the perfect little getaway in Jamaica’s coolest parish. Here you will find tranquility & peace if you’re seeking a perfect relaxation get away. I am very happy to be able to share a piece of my home with you and I am definitely eager to help you create the BEST memories during your stay!

Guest favourite
A view is captured from a balcony framed by an arched opening. Lush palm trees sway gently in the warm breeze, providing a backdrop for the sandy beach and tranquil ocean visible in the distance. Two chairs are positioned on the balcony, inviting relaxation.
Apartment in Ocho Rios
4.83 out of 5 average rating, 143 reviews

Ocho Rios Bay Beach Apartment

This recently refurbished one bedroom apartment sits directly on Ocho Rios bay beach. Located in the heart of the town shops, restaurants, bars are just minutes away. Several major attractions including Dunn’s River Falls, Mystic Mountain and Dolphin Cove are in close proximity. The overall property has a swimming pool and bar that guests may enjoy and is literally steps from the Ocho Rios Bay Beach.

Popular amenities for Middlesex County holiday rentals